I recently signed an offer letter for a new role with a tentative start date of June 22. Since the 26th, my background check and employment verifications have been in progress. I had initially communicated to the recruiter that I would love some time off between jobs, and he assured me that this wouldn’t be a problem, even giving me an extra week. However, I didn’t anticipate the background check and verifications would take this long. Now it's the 30th, and if everything doesn’t wrap up by Monday the 1st, I might end up having to work into the week of the 15th, leaving me with only three days between jobs. I’m leaving my current employer because it has become completely unsustainable for my mental health, and I really wanted that time to process the transition. Both roles are remote, and I hoped to adjust and start the new job in a better headspace. My past employers were all small companies, and I’m worried that the background check might delay the process since they might struggle to contact my previous bosses, especially since one of the companies no longer exists. Now, I’m torn between two options: should I just go ahead and give my two weeks' notice, assuming everything will clear up by Friday? Or should I ask the recruiter if I can push back my start date by another week? I’m really anxious about messing up this opportunity, but I also feel that I need a break. I’ve heard horror stories about job transitions and I’ve been through unemployment before, so I’m really keen to avoid that again. I’m seeking advice on whether asking for an extension would look bad or if it would raise any flags if I say I want to wait until everything is cleared before giving my notice.